Lyconadins G and H, Two Rare Lyconadin-Type <i>Lycopodium</i> Alkaloids from <i>Lycopodium complanatum</i>

doi:10.1007/s13659-016-0111-9

Natural Products and Bioprospecting

2016, Vol. 6

Issue (6) : 279-284 DOI: 10.1007/s13659-016-0111-9

Original article

Lyconadins G and H, Two Rare Lyconadin-Type Lycopodium Alkaloids from Lycopodium complanatum

Jin-Tang Cheng^1,3, Zhi-Jun Zhang¹, Xiao-Nian Li¹, Li-Yan Peng¹, Huai-Rong Luo¹, Xing-De Wu¹, Qin-Shi Zhao^1,2

1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
2. Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100700, People's Republic of China

Abstract
References
Related Articles
Metrics

Download: PDF(882 KB) HTML ()
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks

Abstract Two rare lyconadin-type Lycopodium alkaloids, lyconadins G (1) and H (2), together with four known ones (3-6), were isolated from Lycopodium complanatum. The structures were determined on the basis of their spectroscopic analyses, and the absolute configuration of 1 was established by an X-ray crystallographic analysis. It is the first time to establish the absolute configuration of lyconadin-type Lycopodium alkaloid by an X-ray diffraction experiment. In addition, these findings may provide more information for the biosynthesis of lyconadins.

Keywords Lycopodium alkaloids Lycopodium complanatum Lyconad

Fund:This work was financially supported by the NSFC-Joint Foundation of Yunnan Province (No.U1502223);the National Natural Science Foundation of China (No.21402212);the Science and Technology Program of Yunnan Province (No.2015FB173),and the CAS "Light of West China" Program and Youth Innovation Promotion Association CAS (X.-D.Wu)

Issue Date: 31 January 2018

	Service

	E-mail this article
	E-mail Alert
	RSS
	Articles by authors

	Jin-Tang Cheng
	Zhi-Jun Zhang
	Xiao-Nian Li
	Li-Yan Peng
	Huai-Rong Luo
	Xing-De Wu
	Qin-Shi Zhao

Trendmd:

Cite this article:

Jin-Tang Cheng,Zhi-Jun Zhang,Xiao-Nian Li, et al. Lyconadins G and H, Two Rare Lyconadin-Type Lycopodium Alkaloids from Lycopodium complanatum[J]. Natural Products and Bioprospecting, 2016, 6(6): 279-284.

URL:

http://npb.kib.ac.cn/EN/10.1007/s13659-016-0111-9 OR http://npb.kib.ac.cn/EN/Y2016/V6/I6/279

1. V. Bisai, R. Sarpong, Org. Lett. 12, 2551-2553 (2010)
2. S.M. Canham, D.J. France, L.E. Overman, J. Am. Chem. Soc. 132, 7876-7877 (2010)
3. H.M. Ge, L.D. Zhang, R.X. Tan, Z.J. Yao, J. Am. Chem. Soc. 134, 12323-12325 (2012)
4. T. Nishimura, A.K. Unni, S. Yokoshima, T. Fukuyama, J. Am. Chem. Soc. 135, 3243-3247 (2013)
5. S.Z. Jiang, T. Lei, K. Wei, Y.R. Yang, Org. Lett. 16, 5612-5615 (2014)
6. X. Ma, D.R. Gang, Nat. Prod. Rep. 21, 752-772 (2004)
7. Y. Hirasawa, J. Kobayashi, H. Morita, Heterocycles 77, 679-729 (2009)
8. M. Kitajima, H. Takayama, Top. Curr. Chem. 309, 1-31 (2012)
9. J.S. Liu, Y.L. Zhu, C.M. Yu, Y.Z. Zhou, Y.Y. Han, F.W. Wu, B.F. Qi, Can. J. Chem. 64, 837-839 (1986)
10. Y. Hirasawa, T. Tanaka, K. Koyama, H. Morita, Tetrahedron Lett. 50, 4816-4819 (2009)
11. K. Ishiuchi, S. Kodama, T. Kubota, S. Hayashi, T. Shibata, J. Kobayashi, Chem. Pharm. Bull. 57, 877-881 (2009)
12. F.W. Zhao, Q.Y. Sun, F.M. Yang, G.W. Hu, J.F. Luo, G.H. Tang, Y.H. Wang, C.L. Long, Org. Lett. 12, 3922-3925 (2010)
13. J. He, X.Q. Chen, M.M. Li, Y. Zhao, G. Xu, X. Cheng, L.Y. Peng, M.J. Xie, Y.T. Zheng, Y.P. Wang, Q.S. Zhao, Org. Lett. 11, 1397-1400 (2009)
14. S.G. Lu, G.F. Zhang, W.H. Su, R.X. Wang, C.X. Li, C.D. Xu, X.C. Deng, Y.Q. Duan, Y. Wang, B.B. Zhang, Pteridology (Higher Education Press, Beijing, 2007), pp. 45-47
15. X.D. Wu, J. He, G. Xu, L.Y. Peng, L.D. Song, Q.S. Zhao, Acta Bot Yunnanica. 31, 93-96 (2009)
16. J.T. Cheng, F. Liu, X.N. Li, X.D. Wu, L.B. Dong, L.Y. Peng, S.X. Huang, J. He, Q.S. Zhao, Org. Lett. 15, 2438-2441 (2013)
17. L.B. Dong, X. Gao, F. Liu, J. He, X.D. Wu, Y. Li, Q.S. Zhao, Org. Lett. 15, 3570-3573 (2013)
18. L.B. Dong, Y.N. Wu, S.Z. Jiang, X.D. Wu, J. He, Y.R. Yang, Q.S. Zhao, Org. Lett. 16, 2700-2703 (2014)
19. J. Kobayashi, Y. Hirasawa, N. Yoshida, H. Morita, J. Org. Chem. 66, 5901-5904 (2001)
20. K. Ishiuchi, T. Kubota, H. Ishiyama, S. Hayashi, T. Shibata, J. Kobayashi, Tetrahedron Lett. 52, 289-292 (2011)
21. K. Ishiuchi, T. Kubota, H. Ishiyama, S. Hayashi, T. Shibata, K. Mori, Y. Obara, N. Nakahata, J. Kobayashi, Bioorg. Med. Chem. 19, 749-753 (2011)
22. Z. Wang, J. Wu, N. Zhao, Y. Yang, Y. Chen, Nat. Prod. Res. 30, 241-245 (2016)
23. W.J. Meng, J. Xiong, W.X. Wang, H.Y. Zhang, H. Zeng, J.F. Hu, Tetrahedron Lett. 57, 3218-3221 (2016)
24. W.W. Jiang, Y.C. Liu, Z.J. Zhang, Y.C. Liu, J. He, J. Su, X. Cheng, L.Y. Peng, L.D. Shao, X.D. Wu, J.H. Yang, Q.S. Zhao, Fitoterapia 109, 155-161 (2016)
25. K. Ishiuchi, W.P. Jiang, Y. Fujiwara, J.B. Wu, S. Kitanaka, Bioorg. Med. Chem. Lett. 26, 2636-2640 (2016)
26. K. Ishiuchi, T. Kubota, T. Hoshino, Y. Obara, N. Nakahata, J. Kobayashi, Bioorg. Med. Chem. 14, 5995-6000 (2006)
27. Y. Yang, M. Dai, Synlett 25, 2093-2098 (2014)
28. S.P. West, A. Bisai, A.D. Lim, R.R. Narayan, R. Sarpong, J. Am. Chem. Soc. 131, 11187-11194 (2009)
29. D.C. Beshore, A.B. Smith, J. Am. Chem. Soc. 129, 4148-4149 (2007)
30. I.K. Rhee, N. Appels, B. Hofte, B. Karabatak, C. Erkelens, L.M. Stark, L.A. Flippin, R. Verpoorte, Biol. Pharm. Bull. 27, 1804-1809 (2004)
31. G.L. Ellman, K.D. Courtney, V. Andres Jr., R.M. Featherstone, Biochem. Pharmacol. 7, 88-95 (1961)

No related articles found!

Viewed

Full text

Abstract

Cited

Shared

Discussed